What was the most difficult paycheck you ever earned?
Do you love your work?
Are you satisfied with your current salary?
Have you ever lied to keep your job?
What is something satisfying about your work?
Where is the most interesting destination you got to travel to for business?
What was the dirtiest job you ever did?
How hard do you think you work?
What professions require the skills you have and love?
What work-life issues plague teenagers with jobs?
How many jobs have you had?
Do you think smart kids should skip college to start their own companies?
Would you accept a less enjoyable job for twice what you make?
What has been your motivation to achieve or succeed in your career?
How important is putting in “face time” at work?
Do you display your pet’s picture at work?
What are some false or outdated assumptions people operate under at work?
What was your first self-supporting job?
How can you become more knowledgeable and current in your field?
Would you respect a boss less if he or she smoked cigarettes?
What do you think about the wife as the primary wage-earner?
Have you ever worked for minimum wage when you were over the age of 21?
What new position would you like to attain at work?
How would you deal with the emotional turmoil of losing a job?
As a teenager, what were your part-time jobs?
Have you ever worked as a waiter or waitress?
How can you get paid for doing what you love?
What is an unusual occupation of a friend or relative?
Have you worked mostly with men or women?
Which gender do you prefer as bosses?
Which gender do you prefer as subordinates?
What early jobs did you have?
Do you like to be told what to do or be your own boss?
If you made a huge mistake at work, would you admit it or pretend it had nothing to do with you?
What was the most unusual job you ever had?
On a typical workday, what takes up most of your time?
Have you ever cried at work?
How stressful is your job?
Why should you be hired over other candidates for a job?
How do you advertise yourself?
Are you hardworking or lazy?
What occupation will have the highest salary in fifty years?
What job would you like to have for one month?
Do you have an ultimate career goal?
What would have been your dream career?
What is your idea of the Utopian workplace?
What ideas do you think would help your company improve quality, save money, and increase sales and productivity?
When was a time you lost a job?
How often do you lie at work?
Who would you trade jobs with and why?
Have you ever worked unusual hours?
How do incompetent and obnoxious people manage to keep their jobs?
Of what accomplishments in your career are you the proudest?
What have been the high points of your career(s)?
How much did your first job influence your later career?
What is something you would like to shout at your boss or coworkers?
What is the next challenging assignment you would like to have at work?
What type of work would you like to be doing five years from now?
Which do you prefer to work for: a small company or a giant?
You have striven to be what kind of worker with what qualities?
Do you agree with your employer’s policies and procedures? Have you gone against any of them?
What professions or occupations are actually more harmful than good?
How did your level of education influence your career?
Have you ever been a victim of harassment on the job?
What good business tips have people given you?
What businessperson do you particularly admire?
Does your work keep you awake at night? Why?
What is the simple secret of success in the work world?
What project(s) have you worked on that did not turn out as planned?
Tell a story about a favorite boss.
What promotions have you had?
Have you ever been passed over for a promotion and what did you do about it?
What occupational certifications would you like to achieve?
What kind of company culture and environment are ideal for you?
What additional career education would you like to attain?
What higher educational degrees would you like to achieve?
What business or company do you wish you owned?
Would you like to have your significant other working for you? With you?
Do you have a calling?
What is the most innovative practice, service, or product your organization has launched in the past year?
Where did you get started in your career?
What changes would you like to see made at your company?
What odd jobs have you done?
IF YOU COULD …
… hire a personal assistant, what would he or she do for you?
… have had any job in history, what would it be and why?
… work fewer hours in exchange for less pay, would you?
… choose what hours and days you work, how would you schedule your forty hours?
… trade work skills the way kids swap baseball cards, who would you trade with and for what skills?
… start your own business, what would it be?
… create a new, unique position for yourself in your organization, what it would be?
Have you ever dated anybody you met at work?
Would you take a golden parachute plan?
What unnecessary work interruptions and trivial matters could you do without?
What are the most popular lies people tell at work?
How would you react to having to listen to New Age music at work for motivation?
How might technology affect your job in fifty years?
Have you ever run your own business? How did you start it?
Do you wish you worked more or fewer hours a week?
Who is the most naturally gifted person you have worked with?
Which interests and economic factors led you to certain career choices?
How do you think your mate feels about his or her career?
Have you ever worked at a fast-food restaurant?
Do you enjoy physical work or mental work?
Have you ever taken supplies from work?
Do you prefer to work alone or with a group?
What work assignment(s) have you particularly enjoyed?
Would you be working in a different profession if it paid more?
Do you often have several projects going at once?
How did where you earned your degree influence your career?
In what way has affirmative action affected you?
Have you ever been discriminated against at work?
What is something important on your desk?
Are you working too hard?
What would you want to be if talentwise it was possible?
What are your present major projects and ventures?
At work, do you make most of the decisions?
What job could your company not pay you enough to do?
What would be a practical alternative to business cards?
What should be the minimum number of paid vacation days dictated by the government?
If a female employee is told by a male supervisor that she looks good, is that sexual harassment?
Do you think women have the same opportunities as men to get jobs or be promoted?
Which high position in your government, industry, religion, or education would you want?
If you were a mail carrier, what weather would bother you most?
Have any major setbacks occurred in your career(s)?
Who has helped you up the ladder?
Are you happier working backstage or as the leading actor?
What people do you know who have been laid off or fired in the last economic downturn?
What is your most important work-style quality?
What is the current state of your career?
What about work most reminds you of what you disliked about school?